Why Do Most Digital Nomads Fail to Make it Work?


It’s and warm and sunny or cold and blustery November afternoon, depending on where you are in the world. Inside a private group on Facebook, one of the few places this disparate group can connect, digital nomads comment and debate about the struggles of the lifestyle and, in particular, why so many fail to make the lifestyle work.

Along with the topic of registering as an E-citizen in Estonia and someone doing their Master’s Thesis on digital nomads (it’s a more popular choice than you think), it quickly becomes one of the hottest threads in the group. Everyone seems to have something to say on the matter — even if it’s just a brief hello to a fellow nomad or a few words like ‘not being self-organised’, ‘they just give up’, or ‘cos they spend too much time in Facebook groups’.

It’s clear the topic strikes a nerve with a lot of DNs and wannabe DNs. And even if it doesn’t, it offers a somewhat vital excuse to interact with — albeit in a virtual space — real people. Some commenters are more sure on why people fail than others, but the majority take a softer stance, suggesting it’s due to an array of interacting factors — all dependent on the type of person you are and the circumstances you find yourself in.

Whatever the opinion, as they come directly from the ones actually out there living the lifestyle, the discussion offers a valuable and often sobering insight into the real nature of being a digital nomad. And in many ways, the mode in which it is being brought up and the manner in which it is being discussed does a lot more to answer the question than a blog post or list of bullet points ever could.

That being said, as someone who’s been living the lifestyle for a little over four years and for whom there hasn’t passed a day without wondering where it is all heading, here I’m going to take a stab at condensing the responses into a few general themes. At the very least, it may help to open the discussion up to further debate, and at most, it will reveal some of the hidden truths that ultimately lead to many people ‘failing’, giving up, or simply choosing to return to the 9 to 5.

Living The Instagram Dream

Up there with #vanlife, the digital nomad lifestyle is one of the most Instagrammable lifestyles of all. For the poster, it’s the perfect way to conjure up some quick validation and attention after a long day of wandering around lost and alone in a strange country. And for the consumer, it’s equally as great for escaping the grind and dreaming about what life could be like outside of the same bland four walls and the same suits you see day in day out.

All this Grammin’ and bigging up has lead to a huge gaping void to grow between what people think being a digital nomad is like and the actual reality of it. Of course, no one can really know what it’s like until they do it themselves, but deprived office dwellers are not so inclined to put the time in to do some hard research and find it much easier to be engrossed in and deluded by the cherry-picked illusion — to the point they give up everything and dive straight into it with little mental and physical planning.

The idea is that it’s all going to be relaxing on the beach and cocktails and generating masses of passive income through Adsense or dropshipping. Inevitably though, sooner or later the time comes when they realise it’s much more about immigration issues, convenience food, trying to find decent wifi, and making many hard choices often multiple times a day.

Being The Boss of Yourself

With even people who don’t even have access to running water now being able to own a smartphone, the barrier to entry for being a digital nomad is lower than pretty much any other ‘field’. But even though all you need is a phone, internet connection, and to walk to a cafe to try it out, it far from means you’re qualified or skilled enough to make it work.

It’s so easy to get started that every graduate thinks they can just take some savings along with a copy of the 4 Hour Work Week and a laptop to Bali and make money online. So you’re an aspiring digital nomad? In that case, then, you already have experience in running a business, marketing yourself, managing taxes and finances, dealing with customers remotely, visas, having no fixed address, and generally being a super prolific and ultra-resilient internet entrepreneur/lifestyle designer?

As someone in the Digital Nomads Facebook group pointed out, jumping in the water without knowing how to swim doesn’t make you a swimmer. And as we’re going to explore further, trying to learn how to swim by jumping into the middle of the Pacific ocean — unless you’re a cross between Tim Ferriss and Tony Robbins — somewhat unsurprisingly often always ends up in a spluttering mess.

Classic Burn Out

Few people consider that when they set out to be a digital nomad, they’re trying to combine two very different lifestyles and reconcile them into something that has never, ever been done in history.

In essence, they’re attempting to achieve the flexibility and freedom of a nomadic person, who can roam about freely from place to place, with the independence of a digital entrepreneur, who’s income is not tied to one fixed location and is pretty much infinitely scalable.

This unlimited freedom may sound like the dream to any aspiring digital nomad, especially if they’ve been living with their parents or have just come out of the education system. But having endless choice, from choosing where to have breakfast to which skills to develop to which country to buy a plane ticket to next, quickly becomes old and debilitating — or at the very least annoying and energy-sapping.

Local customs, language barriers, ATMs, buses, sickness, hospitals, insurance; for most people, expectedly, all this is too much to balance while having to spend most of your time in front of the screen trying to start or run a business.

Taking The Road Less Traveled

It’s become so normal to talk about loneliness, even to the point of it being fashionable, that anyone who fancies the DN lifestyle is at risk of underestimating how difficult and, at times, unequivocally soul-shattering it can be.

The impression is that if someone’s talking about it boldly on the internet, and are not just some illiterate paralysed and disconnected mess, then it can’t be that bad. They think loneliness, pffftt, I know what it’s like to be lonely: like when I first moved away for uni and didn’t know anyone, or when I went on that weekend camping trip in the woods and forgot my phone.

But being lonely in a crowd and being lonely when you’re actually on your own are two very different things. When you literally have no one to turn to, not even your parents to argue with or colleagues or peers to look down on, an unstoppable cascade of emotions can come quickly rushing in. What makes it so bad is that it inherently happens when you’re halfway around the world, in a place where no one speaks your language, and when you’re most lost and confused about what you’re doing and where you’re going in life.

It seems this realisation, for a lot of digital nomads, is often the straw that breaks the camels back. It’s important to point out, though, that rather than being inherent to the DN lifestyle, this outcome is more just the result of a complex interplay of factors such as lack of preparation and support, unrealistic expectations, poor emotional resilience, and being in a strange and foreign environment.

As the size and activeness of the Facebook group is a testament too, the DN lifestyle can certainly work. And exactly how people manage to do it will be the focus of the next post. In the meantime, let us all keep posting and commenting —  if not to find more solutions and fix things, to embrace and explore the lifestyle with others who’re finding it equally as difficult and challenging to make it work.

Joseph Pennington is a freelance writer and long-term traveller from the North of England. Connect with him on LinkedIn to find more articles on work, technology, spirituality, and everything in between.